Intramolecular orientation at the micellar interface: Control of norrish type I and type II reactivity of benzoinalkylethers via conformational effects

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18 Citations (Scopus)

Abstract

The photolysis of benzoinalkylethers 1‐5 solubilized in detergents show a significant deviation from the course of reaction in isotropic organic solvents. Remarkable difference in photobehaviour is noticed between the short chain (1‐3) and the long chain (4 and 5) benzoinalkylethers in the micellar media. However, the influence of the micellar media on the photobehaviour of alkyldeoxybenzoins 6 and 7 was small. The importance of ‘cage effect’ in controlling the product distribution was evident from its dependence on the micellar size and on the occupancy number. More importantly, a comparative analysis of the photobehaviour of the ketone 1‐7 reveals that the micellar interface can be used to control the conformations of organic molecules.

Original languageEnglish (US)
Pages (from-to)91-102
Number of pages12
JournalJournal of Physical Organic Chemistry
Volume1
Issue number2
DOIs
StatePublished - 1988
Externally publishedYes

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Photolysis
Ketones
Detergents
Organic solvents
Conformations
reactivity
Molecules
detergents
ketones
photolysis
deviation
products
molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "Intramolecular orientation at the micellar interface: Control of norrish type I and type II reactivity of benzoinalkylethers via conformational effects",
abstract = "The photolysis of benzoinalkylethers 1‐5 solubilized in detergents show a significant deviation from the course of reaction in isotropic organic solvents. Remarkable difference in photobehaviour is noticed between the short chain (1‐3) and the long chain (4 and 5) benzoinalkylethers in the micellar media. However, the influence of the micellar media on the photobehaviour of alkyldeoxybenzoins 6 and 7 was small. The importance of ‘cage effect’ in controlling the product distribution was evident from its dependence on the micellar size and on the occupancy number. More importantly, a comparative analysis of the photobehaviour of the ketone 1‐7 reveals that the micellar interface can be used to control the conformations of organic molecules.",
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AU - Ramamurthy, Vaidhyanathan

PY - 1988

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N2 - The photolysis of benzoinalkylethers 1‐5 solubilized in detergents show a significant deviation from the course of reaction in isotropic organic solvents. Remarkable difference in photobehaviour is noticed between the short chain (1‐3) and the long chain (4 and 5) benzoinalkylethers in the micellar media. However, the influence of the micellar media on the photobehaviour of alkyldeoxybenzoins 6 and 7 was small. The importance of ‘cage effect’ in controlling the product distribution was evident from its dependence on the micellar size and on the occupancy number. More importantly, a comparative analysis of the photobehaviour of the ketone 1‐7 reveals that the micellar interface can be used to control the conformations of organic molecules.

AB - The photolysis of benzoinalkylethers 1‐5 solubilized in detergents show a significant deviation from the course of reaction in isotropic organic solvents. Remarkable difference in photobehaviour is noticed between the short chain (1‐3) and the long chain (4 and 5) benzoinalkylethers in the micellar media. However, the influence of the micellar media on the photobehaviour of alkyldeoxybenzoins 6 and 7 was small. The importance of ‘cage effect’ in controlling the product distribution was evident from its dependence on the micellar size and on the occupancy number. More importantly, a comparative analysis of the photobehaviour of the ketone 1‐7 reveals that the micellar interface can be used to control the conformations of organic molecules.

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